


Following in Dr. Sexy's Cowboy Boots

by riseofthefallenone



Category: Supernatural
Genre: Dr. Sexy marathon, Fluff, M/M, POV Sam Winchester
Language: English
Status: Completed
Published: 2016-04-17
Updated: 2016-04-17
Packaged: 2018-06-02 16:59:10
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,021
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6574468
Author URL: https://archiveofourown.org/users/riseofthefallenone/pseuds/riseofthefallenone
Summary: <blockquote class="userstuff">
              <p>When Sam reaches the limits of his patience with the UST between Dean and Cas, he turns to Dr. Sexy for help.</p>
            </blockquote>





	Following in Dr. Sexy's Cowboy Boots

**Author's Note:**

> This is my first time writing from Sam's POV and I hope you like it as much the super sweet [dr-sexys-cowboy-boots](https://dr-sexys-cowboy-boots.tumblr.com) did! This was a thank you gift for them!

Sam is a patient person. He was able to hold off until he was eighteen before he left the hunting life – even though it would have been _so_ easy to run away (which he did once, but that’s beside the point). He waited _months_ before he made his move on Jess (ignoring the fact that she’s the one who made the move first). And he has been oh so very patient with Dean and Cas to figure their goddamn shit out and _act_ on that – that – whatever the hell it is they have going on between them.

Because as patient as he may be, Sam is anything but blind. Everyone alive, dead, and supernatural can probably see the great big neon sign that is the unresolved whatever-that-is that Dean and Cas have. Does it weird Sam out that his brother is in love (yes, _in love_ ) with an angel? Not even remotely. Sam has seen a lot weirder things in his life than that. Does he find it odd that his skirt-chasing brother could be romantically and sexually attracted to the male vessel for said angel? Hah, fat chance.

The thing about growing up while sharing a hotel room with Dean is that there wasn’t a whole lot that could be hidden from him. Dean had his dalliances with both sexes when he was a teenager before he focused on the fairer sex. Sam is pretty damn sure that the whole reason he’s been playing on one side of the fence he’s straddling is because of their dad. But John is gone and there’s an angel actually living with them that is – Well, Sam doesn’t even know what to call Cas. He’s something to Dean, that’s for sure. And it’s definitely not _just_ a friend.

A friend doesn’t just _do_ all the things that Cas has done for Dean – _because_ of Dean – and not mean more than that to a guy. Sam has actually compiled a list of what Cas has done for them that goes above and beyond the call of friendship. Sometimes even beyond _family_. Some of it is just what Sam has learned from word of mouth after the fact, and some of it he’s been witness to. All of it just _screams_ that there’s more than meets the eye with their relationship and it’s driving him crazy knowing that neither one of them has acted on it.

Honestly, it’s like the two of them are circling each other endlessly. Are they waiting for the other to make the first move? Do they not realize that their feelings are most likely (seriously, it’s like 100% likely at this point) returned?

Well, how lucky for them that they have Sam around. Because Sam has eyes and a decent understanding of human-angel interactions. And as patient as he is, even _his_ patience has a limit. And when his impressive patience comes to an end, Sam starts getting crafty. If they won’t see it themselves, then he’s just going to have to _make_ them see it. In this case, he’s going to take the easiest route; the route he knows best – Dean.

Sam knows Cas pretty well, but he’s not so great with understanding human subtleties. If he wanted Cas to figure this out first, he’d have to say it straight to him. With Dean, saying it to him flat out would just put Dean on the defensive and could ruin everything. Luckily, Sam knows how to work the situation to make Dean realize it on his own. And then, if all goes well, those two will get together and live happily ever after – or, as happily ever after as this messed up universe will allow them.

Now, the only thing that Sam needs to wait for is the right opportunity. He just never expected that Dr. Sexy would be it.

* * *

“Sam!” The bunker is huge and somehow Dean still manages to make his voice heard no matter where anyone is. “Sam, get your butt to the TV room! Now!”

Oh yes, the _TV room_. They didn’t use to have one, but Dean got sick of not having enough space for everyone to sit together and watch TV. They don’t exactly have a lot of people over for show watching very often. In fact, Cas is the only one they do that with – and he actually lives here. But Dean still went and converted one of the spare bedrooms into a rather comfortable looking den.

He made a weekend out of it and pulled out the bed and furniture and put in some massive sofa that he cleaned the hell out of after getting it for free off of Craigslist. With scrap wood from – Actually, Sam doesn’t know where Dean got the wood, but the brought it all in and actually _built_ an entertainment center right into the wall. It’s got shelves for DVDs and knickknacks and it’s basically exactly what you’d expect to find in a normal family’s man cave.

The TV was the only thing Dean actually splurged on. Sam helped with that. They went to town one Saturday night and hit six different pool halls between them just to shark the hell out of anyone playing. With the money they raised together, they were able to afford a nice big ‘smart’ TV. Now they’re saving up for a proper sound system. Dean is hell bent on having surround sound. Sam couldn’t care less, but it’s nice to see Dean passionate about something besides hunting. They all _really_ need some proper non-hunting related hobbies.

In fact, when Dean shouts for him, Sam is in the process of looking for said hobbies. There’s all sorts of things he could do, but he doesn’t have anything specific. Video games don’t interest him and he already reads a lot. Writing was never his strong suit at Stanford. Maybe he’ll take up something artsy? Jess was super into art and he always liked watching her paint. Would doing paint-by-numbers count as a hobby? He’ll have to grab one at the craft store the next time he’s in town.

At Dean’s shout, Sam closes his laptop and gets up from his desk. He takes a moment to stretch before shuffling out of his room. It’s still pretty early in the morning, so he hasn’t even bothered changing out of his pajama pants. The bunker is toasty warm and he’s plenty comfortable in that and a t-shirt. Dean, on the other hand, is wrapped up in his stolen housecoat and slippers. He’s also parked square in the middle of the sofa with a bowl of popcorn in his lap.

“What’s up, Dean?”

His answer is a flourished pointing of the remote at the television. “That, Sammy. _That_ is what’s up.”

Sam doesn’t even look. He knows what’s on TV just from the sound. “I’ve seen Dr. Sexy before. What’s so special about that?”

Dean’s face twists into a frown-pout. He’s really good at those. “It’s a _marathon_ , Sam. That’s what’s special. A whole day of Dr. Sexy’s best story arc ending with the unaired season finale!” Almost immediately he breaks into a wide grin and pats the seat next to him. “My marathon buddy isn’t here today, so you’ve gotta step up.”

While Sam is the beloved little brother, he knows without a doubt that he sure as hell could never take whatever position Cas holds in Dean’s heart. And he _really_ doesn’t want to have to sit and watch Dr. Sexy all day. No matter whether or not it’s the best story arc ever. But – well, Cas has been gone on some heavenly envoy thing for the last few days and Sam feels a little bit bad for Dean about it. He’s been moping on and off while looking for pretty much anything to distract himself with. When his best friend isn’t around, Dean is definitely different.

He’s probably just looking for some company. Dr. Sexy is pretty bad, but Sam can tolerate it for his brother. With a sigh, he sits where Dean directs him and props his feet up on a milk crate. It’s the best they’ve got right now until Dean finds an ottoman he likes enough to add to their rec-room.

“Thanks Sammy.” Dean pats him on the knee before his full focus switches to the TV. “If you’re thirsty, there’s beer in the mini-fridge.”

“It’s barely even ten in the morning.”

Dean flaps his hand at him. “It’s never too early for beer.” He flashes him a grin and puts his finger to his lips. “Now shut up. Cas waits for commercials to ask questions so that we can actually watch the show and bask in the joy that is Dr. Sexy and his number one sexy lady, Dr. Cassandra.”

So, he’s not supposed to talk _during_ the episode, is he? Well, that’s just begging for Sam to defy Dean’s rules right there. “Who is Dr. Cassandra?”

Irritation crosses Dean’s face and he sends a withering glare in his direction. “All you need to know is that she’s his best friend, they’re totally in love, and I’m writing the network a strongly worded letter if the season ends without them getting together.”

Best friends in love with each other? Gee, who does _that_ sound like? Sam rolls his eyes and slumps further down on the couch, making himself comfortable. “Alright, alright. I’ll be quiet.”

True to his promise, Sam doesn’t say anything word – even though Dean has little outbursts every now and then. Usually it’s to call Dr. Sexy an idiot for kissing some other lady doctor/nurse/civilian instead of making out with Dr. Cassandra like he _obviously_ wants to do. Sam isn’t nearly as up to date with the show as Dean is (aka: not even remotely aware of what’s going on), so he really doesn’t actually see how the two of the mare quote-unquote ‘in love’.

Five episodes later, Sam can see it. And it’s giving him a _very_ familiar feeling. No best friend looks at their best friend like that while talking and _not_ have feelings for them. Dr. Cassandra always stands super close to Dr. Sexy whenever she’s talking to him. There’s no need for it, but she does it.

“It’s because she’s one of those super genius awkward ladies.” Dean explains during a commercial break. “She had a crazy sheltered upbringing and she’s still breaking out of her shell. You should’ve seen her before she and Dr. Sexy became best friends. She was worse than this.”

“Worse _how_?”

Dean pauses with a piece of popcorn halfway to his lips. He gets a far off look in his eyes while he stares at a point above the TV, trying to think of something. “I dunno, man. Like – I guess she was like Cas before he defied Heaven and joined Team Free Will, y’know? All robot and proper and bullshit and a puppet of her family, or something. Which, by the way, they hate Dr. Sexy _a lot_ coz they think he’s a _bad influence_ – whatever the fuck that means. But she never used to smile or laugh and now she does it at _least_ once an episode and it’s all thanks to Dr. Sexy.”

Sam has to fight to keep what might be a manic grin off his face. This is it! This is his chance! If Dean can already relate Dr. Cassandra to Cas – which is a hilarious coincidence, by the way – then that makes everything a hundred times easier. It should be a walk in the park to use Dr. Sexy and Dr. Cassandra to convince Dean that he and Cas are in the same boat – sorta. He’s going to need more data. If he’s lucky, maybe there might be more that he can correlate between the two relationships.

Another three episodes and several screaming-for-mercy brain cells later, Sam is convinced that he must be dreaming. This is too good to be true. “So, let me get this straight…”

“Get what straight?” Dean’s voice has every inflection of annoyance possible in it.

Sam sits forward, eyes fixed on the TV while Dr. Sexy shouts at some guys in army fatigues. “Why doesn’t he just leave? The authorities know that Dr. Cas is missing –”

“ _Cassandra_.” He interrupts and Sam fights another smile. “It’s weird when you call her Cas.”

“Sorry.” Hah, no he isn’t. Sam is totally doing it one hundred percent on purpose. “Okay, so they joined Doctors Without Borders together, right? But they accidentally ended up in a warzone and he went and lost Dr. Cas? Sorry, Dr. Cassandra.”

Dean’s glare lessens before he nods. “He didn’t _lose_ her. She got _taken_. She’s a prisoner of war!”

“Right, right. But the authorities have been notified and they’re looking for her now. He’s been told that he can leave and wait for her back home.” Sam gestures at the TV, drawing Dean’s attention back to it. “Why doesn’t he just leave?”

“Because he loves her, _duh_.” Dean rolls his eyes and shakes his head, like this is the simplest thing in the world to understand. “If you loved someone, would you leave them behind in a place like that? It would be like me leaving you to rot in Hell, or –”

Sam puts on his best innocent face. “Or – maybe – like you leaving Cas in Purgatory?” Because he is _well_ aware of the fact that Dean had an out through Benny but he _still_ spent a year carving a bloody path through Purgatory looking for Cas. All because he refused to leave without him.

That strikes a chord in Dean. Sam can see it in his eyes and how he’s suddenly _really_ interested in staring at the TV and not making any kind of look at him. “Yeah, kinda like that, I guess.”

Pointing that out keeps Dean quiet for the rest of the episode. Sam, on the other hand, is just getting started. He’s got one ace up his sleeve here that he’s pretty sure is going to drive Dean insane. “But what about Dr. Anaya?”

Dean actually flinches when Sam names the unofficial ‘love-rival’ that he’s been bitching every other episode. “What about _her_?”

“Well, they’re obviously meant for each other.” He’s playing with dynamite here, but the point _needs_ to be made. “Haven’t you seen the way they are around each other in the ER? They’re totally drawn to each other. It’s – like – she’s his destiny.”

Never has Sam been so delighted to see Dean’s nose crinkle. It crinkles so hard that his nose might never be normal again. “ _Ew_ , Sam! That’s just – no. Fuck that. Dr. Sexy and Dr. Cassandra are meant to be. They’ve been through _way_ too much together for this newbie to steal him away.” He starts shaking his head in the way that parents get when they’re disappointed in their kid. “I thought you were smarter than that, Sammy. Can’t you see that they only brought her in to stir the pot? She doesn’t mean a damn thing to Dr. Sexy.”

Sam sits back and crosses his arms. “I guess we’re just going to have to agree to disagree.”

“Fucking _bullshit_.” Dean puts the almost empty popcorn aside. “Here, hold this, Cas.”

He’s halfway turned to Sam when he stops and turns back around. Even Sam leans around him because, sure enough, Cas is sitting there on the other side of the couch, eyes fixed on the TV. Without even so much as a hello, Cas just starts eating the popcorn. He takes the remote from Dean’s lap and actually turns the TV up.

“ _Dude_.” Dean hisses and snatches the remote back, turning the volume down. “When the hell did you get here? How was the Heaven stuff?”

Cas looks away from the TV, face crumpled in that slightly-annoyed look he always seems to carry. “Two seconds before you handed me the popcorn and Heaven is fine. Now, please be quiet. Dr. Sexy is about to reunite with Dr. Cassandra and I don’t want to miss it.” He looks away from them again, only to make one last jab. “And I need to disagree with you, Sam. Dr. Anaya is nothing more than a hindrance to Dr. Sexy. She openly tries to seduce him in attempts to distract him from his job and she is a detriment to the functionality of the hospital. I suspect she’ll be fired before the end of the season.”

With his back a little straighter and a glow of pride in his face, Dean turns back to Sam with a ‘ _Hah! Take that!_ ’ kind of expression. Sam sticks his tongue out at it and leans forward more to try and engage Cas into the conversation. Maybe he can make _him_ see the light too. “I’m not saying that she’s not being a bitch about things. But do you _really_ think it’s more likely that Dr. Sexy would hook up with Dr. Cassandra than he would Dr. Anaya? I mean, he’s actually _kissed_ Dr. Anaya where he’s barely done more than hug Dr. Cassandra.”

“Does _that_ look like a guy who’s not in love with his best friend?” Dean actually grabs Sam’s face and turns his head to look at the screen. In the episode, Dr. Sexy has finally found Dr. Cassandra and he’s got her in a hug and he’s touching her face. They both look worse for the wear.

“Oh, please. That’s just a trick of the ambiance.”

“Sammy, I’m five seconds away from disowning you.”

“I’m five seconds away from using my grace to make you both shut up.”

That works on keeping them quiet for the span of another episode, during which Dr. Sexy and Dr. Cassandra return to the hospital. Sam could swear that any minute one of them is going to throw the other against the wall for some badly acted soap opera kissing. Dean is completely right about the chemistry between the two, but that doesn’t stop Dr. Sexy from continuing to chase the skirts of every other lady in the hospital. Kind of like a certain brother sitting right next to him.

“Wait.” Sam points suddenly at the screen when someone new walks into the scene. “Who’s that?”

“Dude, that’s Dr. Cassandra’s _brother_.” Dean sighs and shakes his head. “We saw him five episodes ago, Sam. Keep up.”

They watch in silence while the brother tries to convince Dr. Cassandra to leave the hospital. Like Dean mentioned before, he keeps calling Dr. Sexy a _bad influence_. Dean just laughs at it. “I don’t know why they keep bothering to try and get her to leave. They’ve been doing that all season and every single time she picks Dr. Sexy over them.”

“That’s just weird.” Sam sits back and crosses his arms. “Who in their right mind would keep picking their best friend over their family? Family is way more important than Dr. Sexy.”

Cas gives him one hell of a side-eye when Dean stands up during a commercial break, beelining for the mini-fridge. “Perhaps her family is not as great as she once thought they were. She is an excellent Doctor and she’s helping people in that hospital. Her family wants her to go into the private sector.”

Dean laughs and actually has the gall to ruffle Cas’s hair right there in front of Sam as he sits down. “You don’t even know what the private sector _means_ , Cas.”

In response, Sam turns up the volume on the TV to drown them out as they start bickering. That’s par for the course when it comes to watching TV with these two. Sam usually likens them to a old married couple – mostly because they _are_ basically married. They have that whole _profound bond_ thing going on. Once upon a time, Sam was kind of jealous that Dean had such a close relationship with Cas. Now he’s used to it and he’s honestly happy for the two of them. He just wishes that they would realize that they can be happy _together_.

In the next few episodes, having carried them straight through into the late afternoon, shit starts going down. Dr. Cassandra goes through a rough period where she makes some bad decisions and gets into some drugs. She’s a changed lady when she’s on it, but she ends up getting taken in by Dr. Sexy and he totally nurses her back to health. Brings her back to herself. All Sam sees is every instant where Cas wasn’t himself for one reason or another – souls, various methods of manipulation, etc – and Dean was always the one who brought him back to being _him_ again.

“You see that shit, Sam?” Dean gestures sharply at the TV as Dr. Sexy kneels next to Dr. Cassandra in the bathroom with a hand on her face and another on her cheek. “How the _hell_ can you say that Dr.Sexy is in love with Dr. Anaya when he’s obviously gaga for Dr. Cassandra? Are you _blind_?”

“Well it’s not like she’s being manipulated by outside forces or anything.” Sam shrugs and leans against the arm of the couch. “I mean, she could’ve sobered up on her own. What’s so special about having a friend help break the spell? He probably would’ve done the same for Dr. Anaya too.”

Dean shoves his hands into his hair and groans. “Seriously, Sam, what the _fuck_. I can’t believe you right now. She’s sobering up _for_ Dr. Sexy because she loves him. And he loves her. Look, right there. He just told her that he _needs_ her. Who would ever say that to someone who was _just_ a _friend_?”

“I don’t know, Dean.” Sam presses his lips together and glances at him, hoping he’ll take his own hint. Because Dean has told him what he said in the crypt that broke Cas out of Naomi’s control. “Why _would_ someone say that to someone who was _just_ a _friend_?”

And that’s when Cas must piece it all together. Suddenly the other end of the couch is radiating hostility and Sam looks over to find Cas outright _glaring_ at him from behind Dean’s head. He raises an eyebrow and Cas mouths one word. _Stop_. Well now, isn’t _that_ interesting? If Sam is reading things right, he’s fairly certain that this means that Cas knows exactly what he’s doing. And if he knows what he’s doing, then Cas knows what’s up between them.

That begs one question; _why_ hasn’t he acted upon it?

At the next commercial break, Sam shoves the empty popcorn bowl into Dean’s lap. “We need more. _You_ wanted to marathon this show, so _you_ have to make sure that we’re fed.”

“Augh, fine.” Dean kicks him in the shin when he stands up. “If only so I don’t have to listen to you tell _lies_ about Dr. Sexy and Dr. Anaya.”

He’s not gone for more than a few seconds before Sam is turning to Cas. “So.”

“No.” Cas shakes his head and gives Sam one of his _death squints_. “We are not discussing this. There is nothing _to_ discuss. Just stop whatever you’re trying to do.”

“Why?”

There is no answer for that. Cas just narrows the squint and turns away again. He’s gone all stony, like he was when they first met him all those years ago. It irks Sam more than a little bit and he spends the next few minutes staring hard at the side of Cas’s head. Even that doesn’t get him any kind of reaction. When Cas wants to act like a statue, he’s actually very good at it.

Sam sighs and slumps back in his seat. “Is it because you don’t want it to happen? I can understand if you’re not actually – I mean, if it’s just me reading normal angel things wrong then –”

“You earlier assumptions are not incorrect.” Cas’s shoulder slump slightly, but it’s only for a moment and then he straightens them again. “That is all I’m going to say on the matter.”

Well that’s just not very help. “Would you change your mind if I said that I’m pretty sure I’m about to make a breakthrough with Dean?”

“Breakthrough about _what_?”

Of course Dean would choose that exact moment to walk back into the living room with a full bowl of steaming popcorn. It’s only _his_ timing that would be that perfect. Alright, fine. Sam’s going to whip out his trump cards here. If Cas won’t tell him _why_ he doesn’t want Dean to figure things out, then Sam can’t really abide by his request. He wants his big brother to be happy and he’s absolutely, without a shadow of doubt, certain that a relationship between Dean and Cas would give them happiness that they deserve. And that is all the more important when they’re facing a new kind of apocalypse every other year or so.

He plucks up every ounce of courage that he has to face the wrath of an angel here. “I want to put your beliefs about Dr. Cas and Dr. Sexy to the test.”

Dean looks equal parts curious and annoyed. “I’d like to see you try.”

“Would you still say that they’re in love if Dr. Cas was a man?”

There’s something vindictively sweet to be had in this moment. Dean’s eyes go wide and he opens his mouth, but he doesn’t say anything. Obviously he hasn’t thought this through. He ends up frowning and looking at the screen,  staring at it as hard as he does any puzzle that’s confusing him. Cas is outright glaring at Sam again.

“Let me elaborate, if I may.” Sam clears his throat and lifts his head a little higher. This is his coup de grâce right here and he starts it off by listing every single similarity he’s found between the Doctors’ relationship and Dean and Cas’s relationship. Only, this time around, Sam is vague about it. He doesn’t even talk about what Dr. Sexy and Dr. Cassandra have gone through. His list is completely built from what Cas and Dean have gone through.

By the time he’s done, Dean is staring at him again. Has he _still_ not picked up the clues being laid down here? He’s the one who actually _lived_ through these things. Sam has only learned about half of them after the fact. And he knows that Dean isn’t this dense. He should be – Yup, there it is.

“Well, I’m heading back to my room now.” Sam stands up quickly and ducks past Dean the long way around so he’s staying out of Cas’s reach. “That’s enough Dr. Sexy for me tonight. Night guys!”

He shuts the door behind him and hesitates. It would be rude to stick around and listen, but Sam has been patient long enough. Not to mention that he just spent the whole damn day watching _Dr. Sexy_ just for this one opportunity. Sam _deserves_ to stay with his ear to the door to see what the results of all his hard work is going to amount to.

At first all he hears is the TV, and then Cas’s speaks. “The next episode is going to start soon. Are you going to sit down and watch it with me?”

Dean doesn’t answer. At least not with words that Sam can hear. Instead, it’s another bout of silence and then Cas speaking again. “I realize that it’s hypocritical of me to say this, but having you stare at me like that is rather unnerving.”

 _Finally_ , Dean says something. “They – I mean – Even if she was a he – They’d definitely still be – It’s totally cool for them to be, y’know, gay and everything. I don’t care about that kinda stuff.”

“I know you don’t, Dean. You’re a very accepting person.” There’s a smile in Cas’s voice. “After all I’ve done, you’ve still accepted me as a part of your family. For which I am eternally grateful.”

There’s an even longer silence after that where Sam can’t help but wonder if they’ve finished talking. Dean has never been the greatest about the heart to heart talks. Especially when there’s a chance that he might very well end up hurt. But Sam is positive that nothing is going to hurt Dean here. Cas loves him and he’d never hurt him in the way that Dean would be afraid of.

His back is starting to get sore from being hunched over against the door by the time Dean says anything else. “Do you – did you – I think Sam was trying to make a point about – Y’know, about two people that – that aren’t from the show. If – Do you know what I mean?”

“Yes, Dean, I understand what you mean.” Cas sighs and Sam can almost feel his glare through the door again. “And I am well aware of what Sam was trying to insinuate.”

“And...?”

Silence.

Now that’s just _unfair_. Sam wants to know what’s going on!

He nearly drops to his knees in relief when Cas finally says something again. “I can only speak for myself. But – Well, Sam isn’t _wrong_. Not about me, at least.”

Dean clears his throat after a solid minute of silence again. “He – um – He’s not wrong at all.”

“Oh.” Cas actually sounds surprised. And then the smile is back in his voice. “Would you like to sit with me and watch the season finale, Dean?”

“I’d like that.”

The grin Sam wears all the way to his bedroom is wide enough that it actually hurts. Things are going to be different in their little family now, but he’s plenty happy to see how that’s going to happen. Whatever happens, it’s worth it. Dean and Cas are some of the most deserving people Sam knows to have love in their lives and he can’t wait for the them to find it in each other.

He’s going to have to write a thank you letter to Dr. Sexy for this. If it wasn’t for him and his horrifically soap opera life story, this would have taken even longer to happen – if ever.

Maybe matchmaking should be Sam’s new hobby?


End file.
